Water → N-(3-{5-[3-(acetamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)acetamide

HRID 49567Notes

Reaction equation

HRID 49567 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]([NH:12][CH2:13][C:14]#[CH:15])(=[O:11])[CH3:10].[OH2:16]>C(NC(C)C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:9]([NH:12][CH2:13][C:14]#[C:15][C:5]1[CH:6]=[CH:7][C:2]([C:6]#[C:7][CH2:2][NH:3][C:4](=[O:16])[CH3:5])=[N:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 962WaterHCID 693532,5-DibromopyridineHCID 24079665881-41-6

Product 1

HCID 11369220N-(3-{5-[3-(acetamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)acetamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolvent2×

Procedure

A mixture of 2,5-dibromopyridine (15.0 g, 63.9 mmol), N-acetyl-propargylamine (15.51 g), and PdCl2(PPh3)2 (453 mg) in diisopropylamine (510 mL) was refluxed for 3 hours under a nitrogen atmosphere. To the mixture was added water (200 ml) and diisopropylamine was removed from the mixture by distillation under reduced pressure. The resulting suspension was aged at ambient temperature for 1 hour, and precipitates were collected by filtration and dried under reduced pressure to provide 2-1 (14.0 g).

Workup

  1. temperaturewas refluxed for 3 hours under a nitrogen atmosphere
  2. customwas removed from the mixture by distillation under reduced pressure
  3. customprecipitates
  4. filtrationwere collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8ad80f74f0d945eda0a96eff36b0cfd6
Source dataset
uspto-grants-2004_03
Patent number
US06706885B2

Reaction notes

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